title: Efficient, enantioselective assembly of silanediol protease inhibitors.
abstract: A five-step assembly of silicon-protected dipeptide mimics from commercially available reagents is described. This methodology makes silanediol protease inhibitors readily available for the first time. The sequence features asymmetric hydrosilylation, a novel reduction of a silyl ether to a silyllithium reagent, and addition of this dianion to a sulfinimine, to produce the complete inhibitor skeleton with full control of stereochemistry. Oxidation of the primary alcohol to an acid completes the synthesis.
authors.affiliation: Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania 19122, United States.
authors.forename: Yingjian
authors.initials: Y
authors.lastname: Bo
authors.forename: Swapnil
authors.initials: S
authors.lastname: Singh
authors.forename: Hoan Quoc
authors.initials: HQ
authors.lastname: Duong
authors.forename: Cui
authors.initials: C
authors.lastname: Cao
authors.forename: Scott McN
authors.initials: SM
authors.lastname: Sieburth
mesh_terms: D040761:Biomimetic Materials / Q000138:chemical synthesis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011480:Protease Inhibitors / Q000138:chemical synthesis*; D012821:Silanes / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D011480:Protease Inhibitors; D012821:Silanes; C475536:silanediol